Water → HCID 10870340, 화합물

HRID 2309577노트

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HRID 2309577 반응식
[NH2:1][C:2]1[S:3][CH:4]=[C:5](/[C:7](=[N:17]/[OH:18])/[C:8]([O:10]CCS(C)(=O)=O)=[O:9])[N:6]=1.Br[CH2:20][C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22].O.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O.C(OCC)(=O)C>[NH2:1][C:2]1[S:3][CH:4]=[C:5](/[C:7](=[N:17]/[O:18][CH2:20][C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])/[C:8]([OH:10])=[O:9])[N:6]=1

참가 물질

7

반응물 4

HCID 962Water2회HCID 11430Potassium CarbonateHCID 79177tert-Butyl bromoacetateHCID 88404401HCID 88404401, 화합물

생성물 1

HCID 10870340HCID 10870340, 화합물수율 87.6%

시약·촉매·용매 2

HCID 180Acetone용매HCID 8857Ethyl Acetate용매

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온도
40 °C

실험 절차

In 200 ml of acetone was suspended 10 g (0.0341 mole) of methylsulfonylethyl 2-(2-aminothiazol-4-yl)-(Z)-2-hydroxyiminoacetate as obtained in Example 3. After a serial addition of 9.98 g (0.0512 mole) of t-butyl bromoacetate, 0.6 ml of water and 18.85 g of anhydrous potassium carbonate, the mixture was stirred at 40° C. for 2 hours followed by addition of 200 ml of water. The mixture was stirred at 30°-35° C. for about an hour, whereby the methylsulfonylethyl group was hydrolytically eliminated. Then, the ethyl acetate was added to the hydrolysis reaction mixture. The organic layer was extracted with water and the aqueous layers were combined and adjusted to pH 2 with 2N HCl. The resulting white crystalline precipitate was collected by filtration and dried to give 9.0 g of 2-(2-aminothiazol-4-yl)-(Z)-2-(t-butoxycarbonylmethoxyimino)acetic acid. (Yiled, 87.6%)

후처리

  1. customas obtained in Example 3
  2. stirringThe mixture was stirred at 30°-35° C. for about an hour
  3. extractionThe organic layer was extracted with water
  4. filtrationThe resulting white crystalline precipitate was collected by filtration
  5. customdried

출처 및 근거

ORD 기록
ord-5c00776934904c36ba2fc0d6bd25770a
출처 데이터셋
uspto-grants-1987_09
특허 번호
US04695639

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